Triethylamine → HCID 178426288, compound

HRID 1987368Notes

Reaction equation

HRID 1987368 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=3)[N:9]2[CH2:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]#[N:26])=[N:4][CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.[NH2:37][OH:38].O>CO.O>[CH3:20][C:19]1[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][CH:8]([C:3]3[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]2[CH2:21][C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[C:25]([NH:37][OH:38])=[NH:26])=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22235265Hydroxylamine monohydrateHCID 674203573-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-benzonitrile

Product 1

HCID 178426288HCID 178426288, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.117 g, 0.31 mmol) in MeOH (3.0 mL)was added Et3N (0.14 mL, 1.00 mmol) followed by NH2OH.H2O (0.070 g, 1.01 mmol). The resultant mixture was stirred at room temperature overnight. The mixture was diluted with water (5 mL) and extracted with CH2Cl2 (5×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH) provided 113 mg (88%) of COMPOUND 71 as a white solid. 1H NMR (CDCl3) δ 1.50-1.72 (m, 3H), 1.94-2.19 (m, 3H), 2.40 (s, 6H), 3.40 (s, 2H), 3.97 (d, 2H, J=9.3 Hz), 5.75 (br s, 2H), 6.37 (d, 1H, J=7.5 Hz), 6.71 (dd, 1H, J=7.5, 7.5 Hz), 6.89 (dd, 2H, J=7.5, 4.8 Hz), 7.19 (d, 1H, J=8.1 Hz), 7.26-7.29 (m, 2H), 7.42 (s, 1H), 8.30 (d, 2H, J=3.9 Hz); ES-MS m/z 416 (M+H).

Workup

  1. extractionextracted with CH2Cl2 (5×10 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification of the crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-54ed7884ce7a47beaad8ab0db8cb735e
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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